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Brønsted Acid/Lewis Base Hybrid Complexes

  • Manabu Hatano
  • Kazuaki IshiharaEmail author
Chapter
Part of the Topics in Organometallic Chemistry book series (TOPORGAN, volume 62)

Abstract

Recent progress on our Brønsted acid/Lewis base hybrid complexes in some asymmetric catalyses is reviewed. Based on the rational design of conjugated acid–base catalysts, tailor-made supramolecular catalysts can show remarkable catalytic activity and higher-ordered selectivities that cannot be realized by ready-made single-molecule catalysts. The chiral supramolecular magnesium(II) binaphtholate complexes trigger the highly enantioselective 1,4-hydrophosphinylation and 1,2-hydrophosphonylation of α,β-unsaturated carbonyl compounds, direct Mannich-type reaction, and hetero-Diels–Alder reaction. Moreover, the advanced supramolecular catalysts are prepared in situ from chiral 3,3′-disubstituted binaphthols and biphenols, arylboronic acid, and B(C6F5)3, for promoting the anomalous endo-/exo-selective Diels–Alder reaction. The specific mechanism and deep insights into the possible key intermediates are discussed on the basis of rational design of chiral supramolecular Brønsted acid/Lewis base hybrid catalysts as artificial enzymes.

Keywords

Acid–base catalyst BINOL Boron Magnesium Supramolecular catalyst 

Abbreviations

acac

Acetylacetonate

BINOL

1,1′-Bi-2-naphthol

Boc

tert-Butoxycarbonyl

cod

Cyclooctadiene

DABCO

1,4-Diazabicyclo[2.2.2]octane

DMF

N,N-Dimethylformamide

MS

Molecular sieves

TBHP

tert-Butyl hydroperoxide

Tf

Trifluoromethanesulfonyl

THF

Tetrahydrofuran

Ts

Toluenesulfonyl

References

  1. 1.
    Lehn JM (1985) Science 227:849CrossRefGoogle Scholar
  2. 2.
    Chen Y, Yekta S, Yudin AK (2003) Chem Rev 103:3155CrossRefGoogle Scholar
  3. 3.
    Brunel JM (2005) Chem Rev 105:857CrossRefGoogle Scholar
  4. 4.
    Holmes IP, Kagan HB (2000) Tetrahedron Lett 41:7453CrossRefGoogle Scholar
  5. 5.
    Nakajima M, Orito Y, Ishizuka T, Hashimoto S (2004) Org Lett 6:3763CrossRefGoogle Scholar
  6. 6.
    Hatano M, Ikeno T, Miyamoto T, Ishihara K (2005) J Am Chem Soc 127:10776CrossRefGoogle Scholar
  7. 7.
    Hatano M, Horibe T, Ishihara K (2010) J Am Chem Soc 132:56CrossRefGoogle Scholar
  8. 8.
    Ichibakase T, Nakajima M (2011) Org Lett 13:1579CrossRefGoogle Scholar
  9. 9.
    Tanaka K, Kukita K, Ichibakase T, Kotani S, Nakajima M (2011) Chem Commun 47:5614CrossRefGoogle Scholar
  10. 10.
    Kotani S, Kukita K, Tanaka K, Ichibakase T, Nakajima M (2014) J Org Chem 79:4817CrossRefGoogle Scholar
  11. 11.
    Bolm C, Beckmann O, Cosp A, Palazzi C (2001) Synlett 2001:1461CrossRefGoogle Scholar
  12. 12.
    Ward DE, Souweha MS (2005) Org Lett 7:3533CrossRefGoogle Scholar
  13. 13.
    Du H, Zhang X, Wang Z, Bao H, You T, Ding K (2008) Eur J Org Chem 2248Google Scholar
  14. 14.
    Hatano M, Horibe T, Ishihara K (2010) Org Lett 12:3502CrossRefGoogle Scholar
  15. 15.
    Hatano M, Ishihara K (2010) Synthesis 2010:3785CrossRefGoogle Scholar
  16. 16.
    Bao H, Wu J, Li H, Wang Z, You T, Ding K (2010) Eur J Org Chem 2010:6722CrossRefGoogle Scholar
  17. 17.
    Lin L, Zhang J, Ma X, Fu X, Wang R (2011) Org Lett 13:6410CrossRefGoogle Scholar
  18. 18.
    Shibasaki M, Sasai H, Arai T (1997) Angew Chem Int Ed Engl 36:1236CrossRefGoogle Scholar
  19. 19.
    Kanai M, Kato N, Ichikawa E, Shibasaki M (2005) Synlett 2005:1491CrossRefGoogle Scholar
  20. 20.
    Shibasaki M, Kanai M, Matsunaga S, Kumagai N (2009) Acc Chem Res 42:1117CrossRefGoogle Scholar
  21. 21.
    Ishihara K, Sakakura A, Hatano M (2007) Synlett 2007:686CrossRefGoogle Scholar
  22. 22.
    Ishihara K (2009) Proc Jpn Acad Ser B 85:290CrossRefGoogle Scholar
  23. 23.
    Engel R (1977) Chem Rev 77:349CrossRefGoogle Scholar
  24. 24.
    Kafarskia P, Lejczaka B (1991) Phosphorus Sulfur Silicon Relat Elem 63:193CrossRefGoogle Scholar
  25. 25.
    Seto H, Kuzuyama T (1999) Nat Prod Rep 16:589CrossRefGoogle Scholar
  26. 26.
    Fields SC (1999) Tetrahedron 55:12237CrossRefGoogle Scholar
  27. 27.
    Albrecht Ł, Albrecht A, Krawczyk H, Jørgensen KA (2010) Chem Eur J 16:28CrossRefGoogle Scholar
  28. 28.
    Sobhani S, Tashrifi Z (2010) Tetrahedron 66:1429CrossRefGoogle Scholar
  29. 29.
    Helmchen G, Pfaltz A (2000) Acc Chem Res 33:336CrossRefGoogle Scholar
  30. 30.
    Tang W, Zhang X (2003) Chem Rev 103:3029CrossRefGoogle Scholar
  31. 31.
    Guiry PJ, Saunders CP (2004) Adv Synth Catal 346:497CrossRefGoogle Scholar
  32. 32.
    Benaglia M, Rossi S (2010) Org Biomol Chem 8:3824CrossRefGoogle Scholar
  33. 33.
    Kolodiazhnyi OI (2005) Tetrahedron Asymmetry 16:3295CrossRefGoogle Scholar
  34. 34.
    Enders D, Saint-Dizier A, Lannou MI, Lenzen A (2006) Eur J Org Chem 2006:29CrossRefGoogle Scholar
  35. 35.
    Merino P, Marqués-López E, Herrera RP (2008) Adv Synth Catal 350:1195CrossRefGoogle Scholar
  36. 36.
    Zhao D, Wang R (2012) Chem Soc Rev 41:2095CrossRefGoogle Scholar
  37. 37.
    Zhou X, Liu Y, Chang L, Zhao J, Shang D, Liu X, Lin L, Feng X (2009) Adv Synth Catal 351:2567CrossRefGoogle Scholar
  38. 38.
    Uraguchi D, Ito T, Nakamura S, Ooi T (2010) Chem Sci 1:488CrossRefGoogle Scholar
  39. 39.
    Zhou X, Zhang Q, Hui Y, Chen W, Jiang J, Lin L, Liu X, Feng X (2010) Org Lett 12:4296CrossRefGoogle Scholar
  40. 40.
    Sasai H, Arai S, Tahara Y, Shibasaki M (1995) J Org Chem 60:6656CrossRefGoogle Scholar
  41. 41.
    Arai T, Bougauchi M, Sasai H, Shibasaki M (1996) J Org Chem 61:2926CrossRefGoogle Scholar
  42. 42.
    Gröger H, Saida Y, Arai S, Martens J, Sasai H, Shibasaki M (1996) Tetrahedron Lett 37:9291CrossRefGoogle Scholar
  43. 43.
    Sasai H, Bougauchi M, Arai T, Shibasaki M (1997) Tetrahedron Lett 38:2717CrossRefGoogle Scholar
  44. 44.
    Gröger H, Saida Y, Sasai H, Yamaguchi K, Martens J, Shibasaki M (1998) J Am Chem Soc 120:3089CrossRefGoogle Scholar
  45. 45.
    Schlemminger I, Saida Y, Gröger H, Maison W, Durot N, Sasai H, Shibasaki M, Martens J (2000) J Org Chem 65:4818CrossRefGoogle Scholar
  46. 46.
    Mastryukova TA, Aladzheva IM, Leont’eva IV, Petrovski PV, Fedin EI, Kabachnik MI (1980) Pure Appl Chem 52:945CrossRefGoogle Scholar
  47. 47.
    Li J-N, Liu L, Fu Y, Guo Q-X (2006) Tetrahedron 62:4453CrossRefGoogle Scholar
  48. 48.
    Hatano M, Horibe T, Ishihara K (2013) Angew Chem Int Ed 52:4549CrossRefGoogle Scholar
  49. 49.
    Sekine M, Nakajima M, Kume A, Hashizume A, Hata T (1982) Bull Chem Soc Jpn 55:224CrossRefGoogle Scholar
  50. 50.
    Maeda H, Takahashi K, Ohmori H (1988) Tetrahedron 54:12233CrossRefGoogle Scholar
  51. 51.
    Hatano M, Suzuki S, Takagi E, Ishihara K (2009) Tetrahedron Lett 50:3171CrossRefGoogle Scholar
  52. 52.
    Gilbertson SR, Chang C-WT (1997) Chem Commun 1997:975CrossRefGoogle Scholar
  53. 53.
    Sakakura A, Kondo R, Ishihara K (2005) Org Lett 7:1971CrossRefGoogle Scholar
  54. 54.
    Sakakura A, Kondo R, Umemura S, Ishihara K (2007) Adv Synth Catal 349:1641CrossRefGoogle Scholar
  55. 55.
    Sakakura A, Kondo R, Umemura S, Ishihara K (2009) Tetrahedron 65:2102CrossRefGoogle Scholar
  56. 56.
    Wróblewski AE (1983) Tetrahedron 39:1809CrossRefGoogle Scholar
  57. 57.
    Garaev RS (1995) Pham Chem J 29:87CrossRefGoogle Scholar
  58. 58.
    Mashiko T, Kumagai N, Shibasaki M (2009) J Am Chem Soc 131:14990CrossRefGoogle Scholar
  59. 59.
    Sasai H, Arai T, Shibasaki M (1994) J Am Chem Soc 116:1571CrossRefGoogle Scholar
  60. 60.
    Hatano M, Horibe T, Yamashita K, Ishihara K (2013) Asian J Org Chem 2:952CrossRefGoogle Scholar
  61. 61.
    Kagan HB, Riant O (1992) Chem Rev 92:1007CrossRefGoogle Scholar
  62. 62.
    Waldmann H (1994) Synthesis 1994:535CrossRefGoogle Scholar
  63. 63.
    Jørgensen KA (2000) Angew Chem Int Ed 39:3558CrossRefGoogle Scholar
  64. 64.
    Jørgensen KA (2004) Eur J Org Chem 2004:2093CrossRefGoogle Scholar
  65. 65.
    Pellissier H (2009) Tetrahedron 65:2839CrossRefGoogle Scholar
  66. 66.
    Pellissier H (2012) Tetrahedron 68:2197CrossRefGoogle Scholar
  67. 67.
    Corey EJ (2002) Angew Chem Int Ed 41:1650CrossRefGoogle Scholar
  68. 68.
    Nicolaou KC, Snyder SA, Montagnon T, Vassilikogiannakis G (2002) Angew Chem Int Ed 41:1668CrossRefGoogle Scholar
  69. 69.
    Merino P, Marqués-López E, Tejero T, Herrera RP (2010) Synthesis 2010:1CrossRefGoogle Scholar
  70. 70.
    Du H, Ding K (2010) In: Ma S (ed) Handbook of cyclization reactions. Wiley-VCH, Stuttgart, pp 1–57Google Scholar
  71. 71.
    Ishihara K, Sakakura A (2011) In: Evans PA (ed) Science of synthesis, stereoselective synthesis, vol 3. Thieme, Weinheim, pp 67–123Google Scholar
  72. 72.
    Hoffmann R, Woodward RB (1965) J Am Chem Soc 87:4388CrossRefGoogle Scholar
  73. 73.
    García JI, Mayoral JA, Salvatella L (2000) Acc Chem Res 33:658CrossRefGoogle Scholar
  74. 74.
    Barba C, Carmona D, García JI, Lamata MP, Mayoral JA, Salvatella L, Viguri F (2006) J Org Chem 71:9831CrossRefGoogle Scholar
  75. 75.
    Wannere CS, Paul A, Herges R, Houk KN, Schaefer HF III, von Ragué SP (2007) J Comp Chem 28:344CrossRefGoogle Scholar
  76. 76.
    Maruoka K, Imoto H, Yamamoto H (1994) J Am Chem Soc 116:12115CrossRefGoogle Scholar
  77. 77.
    Kündig EP, Saudan CM, Alezra V, Viton F, Bernardinelli G (2001) Angew Chem Int Ed 40:4481CrossRefGoogle Scholar
  78. 78.
    Sibi MP, Nie X, Shackleford JP, Stanley LM, Bouret F (2008) Synlett 2008:2655CrossRefGoogle Scholar
  79. 79.
    Kano T, Tanaka Y, Maruoka K (2006) Org Lett 8:2687CrossRefGoogle Scholar
  80. 80.
    Kano T, Tanaka Y, Maruoka K (2007) Chem Asian J 2:1161CrossRefGoogle Scholar
  81. 81.
    Hayashi Y, Samanta S, Gotoh H, Ishikawa H (2008) Angew Chem Int Ed 47:6634CrossRefGoogle Scholar
  82. 82.
    Hamashima Y, Sawada D, Kanai M, Shibasaki M (1999) J Am Chem Soc 121:2641CrossRefGoogle Scholar
  83. 83.
    Takamura M, Hamashima Y, Usuda H, Kanai M, Shibasaki M (2000) Angew Chem Int Ed 39:1650CrossRefGoogle Scholar
  84. 84.
    Kanai M, Hamashima Y, Shibasaki M (2000) Tetrahedron Lett 41:2405CrossRefGoogle Scholar
  85. 85.
    Takamura M, Funabashi K, Kanai M, Shibasaki M (2000) J Am Chem Soc 122:6327CrossRefGoogle Scholar
  86. 86.
    Hamashima Y, Kanai M, Shibasaki M (2000) J Am Chem Soc 122:7412CrossRefGoogle Scholar
  87. 87.
    Funabashi K, Ratni H, Kanai M, Shibasaki M (2001) J Am Chem Soc 123:10784CrossRefGoogle Scholar
  88. 88.
    Morimoto H, Yoshino T, Yukawa T, Lu G, Matsunaga S, Shibasaki M (2008) Angew Chem Int Ed 47:9125CrossRefGoogle Scholar
  89. 89.
    Yamatsugu K, Yin L, Kamijo S, Kimura Y, Kanai M, Shibasaki M (2009) Angew Chem Int Ed 48:1070CrossRefGoogle Scholar
  90. 90.
    Yazaki R, Kumagai N, Shibasaki M (2010) J Am Chem Soc 132:5522CrossRefGoogle Scholar
  91. 91.
    Yazaki R, Kumagai N, Shibasaki M (2010) J Am Chem Soc 132:10275CrossRefGoogle Scholar
  92. 92.
    Yazaki R, Kumagai N, Shibasaki M (2011) Chem Asian J 6:1778CrossRefGoogle Scholar
  93. 93.
    Yanagida Y, Yazaki R, Kumagai N, Shibasaki M (2011) Angew Chem Int Ed 50:7910CrossRefGoogle Scholar
  94. 94.
    Hatano M, Miyamoto T, Ishihara K (2005) Adv Synth Catal 347:1561CrossRefGoogle Scholar
  95. 95.
    Hatano M, Miyamoto T, Ishihara K (2006) Synlett 2006:1762CrossRefGoogle Scholar
  96. 96.
    Hatano M, Miyamoto T, Ishihara K (2006) J Org Chem 71:6474CrossRefGoogle Scholar
  97. 97.
    Hatano M, Ishihara K (2008) Chem Rec 8:143CrossRefGoogle Scholar
  98. 98.
    Hatano M, Mizuno T, Ishihara K (2010) Chem Commun 46:5443CrossRefGoogle Scholar
  99. 99.
    Hatano M, Mizuno T, Ishihara K (2010) Synlett 2010:2024CrossRefGoogle Scholar
  100. 100.
    Hatano M, Mizuno T, Ishihara K (2011) Tetrahedron 67:4417CrossRefGoogle Scholar
  101. 101.
    Hatano M, Gouzu R, Mizuno T, Abe H, Yamada T, Ishihara K (2011) Catal Sci Technol 1:1149CrossRefGoogle Scholar
  102. 102.
    Hatano M, Mizuno T, Izumiseki A, Usami R, Asai T, Akakura M, Ishihara K (2011) Angew Chem Int Ed 50:12189CrossRefGoogle Scholar
  103. 103.
    Hatano M, Ishihara K (2012) Chem Commun 48:4273CrossRefGoogle Scholar
  104. 104.
    Ishihara K, Kurihara H, Matsumoto M, Yamamoto H (1998) J Am Chem Soc 120:6920CrossRefGoogle Scholar
  105. 105.
    Beckett MA, Brassington DS, Light ME, Hursthouse MB (2001) J Chem Soc Dalton Trans 2001:1768CrossRefGoogle Scholar
  106. 106.
    Ishihara K, Kobayashi J, Inanaga K, Yamamoto H (2001) Synlett 2001:394CrossRefGoogle Scholar
  107. 107.
    Futatsugi K, Yamamoto H (2005) Angew Chem Int Ed 44:1484CrossRefGoogle Scholar
  108. 108.
    Corey EJ, Loh T-P (1991) J Am Chem Soc 113:8966CrossRefGoogle Scholar
  109. 109.
    Corey EJ, Loh T-P (1993) Tetrahedron Lett 34:3979CrossRefGoogle Scholar
  110. 110.
    Sprott KT, Corey EJ (2003) Org Lett 5:2465CrossRefGoogle Scholar

Copyright information

© Springer International Publishing Switzerland 2015

Authors and Affiliations

  1. 1.Graduate School of EngineeringNagoya UniversityChikusaJapan

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